I Tried Daily Coaching with GoalsWon. Here’s What Happened

Can Digital Coaching Really Help With My Goals? Here's What I Learned From My GoalsWon Test

I recently completed a three-week GoalsWon coaching pilot (courtesy of Goalswon), and what I learned surprised me. In this article, I'm sharing my exact goals, process, and results: what happened during and after 21 days (the often-cited window for habit formation) of daily accountability and support from a real human coach paired with a goal-tracking app.

Have you ever tried coaching? Over the years, I’ve worked with many: life, business, startup, and executive. I’ve also experimented with digital coaching apps like Headspace (the coaching version, not the meditation one) and even built my own AI coach called GoalDigger using ChatGPT. So, when I started the GoalsWon program, I was curious: could this model help me reach my high-priority goals in a more consistent, sustainable way?

As someone currently earning my Health and Wellness Coaching credential, I saw it as both a growth experiment and a professional study in being coached virtually—daily, in real time, with another human guiding the process. GoalsWon starts with a 7-day free trial to help you meet your coach, explore the app, and see if it’s the right fit.

Jump to:

Key Takeaways & Value
Who Are the Coaches at GoalsWon
What Goals Can You Set in the GoalsWon Coaching App
My Three Goals for the 21-Day Coaching Experiment
How Goals Are Achieved with GoalsWon
Holiday Mode and Rest Days
Data-Driven Coaching Insights
Visual Progress and Motivation
My Results After 3 Weeks
Wins & Celebrations
GoalsWon vs Headspace vs ChatGPT Coaching
App Experience
Bottom Line
About the Author

Who Are The Coaches At GoalsWon

My coaching experience at GoalsWon started with meeting my coach, Divina.

Divina is a psychology graduate working on her master's degree. She plays volleyball in her free time and enjoys cozy, relaxing weekends, just like me. She is based in Tokyo and I’m in California, so there was a bit of a time difference. She shared her calendar so I could easily book an introductory call.

During our onboarding call, I shared a bit about myself and my goals for the month, and I had the opportunity to ask Divina questions about the program.

Divina also shared the onboarding video, which provides a clear overview of the program and app features. She helped me set up my profile and get more clarity on my top three goals for the month using the SMART framework (specific, measurable, attainable, relevant, time-bound). This approach transforms vague ideas into actionable plans, offering better structure and support.

What Goals Can You Set with GoalsWon?

There are three kinds of coaching goals and targets you can set in GoalsWon.

Daily goals are tasks and behaviors we set and track each day. They are the foundation of the system and support monthly targets.

For example, prepare my gym bag the night before and workout at the gym after work.

Monthly goals: These targets should be SMART goals—Specific, Measurable, Attainable, Relevant, and Time-bound.

For example, increase strength by weightlifting three times a week and tracking progress using my fitness app, along with a monthly in-body scan for body composition analysis.

Annual goals (new!): these are North Star goals serving as direction and vision for the year. They do not have to be as specific and can be a theme. From yearly goals, we set our monthly targets.

For example, write my first book and create a book launch strategy.

My Three Goals for the 21-Day Coaching Experiment

I decided to focus on the following three monthly goals, each of which I needed an extra boost to accomplish:

Goal #1 — Grow My Book Community (Creative Goal)
Goal #2 — Rebuild My Morning Routine (Wellness Goal)
Goal #3 — Get Stronger at the Gym (Fitness Goal)

Goal #1: Book Launch and Community Growth Goal

More specifically, grow my book’s early reader community to 500 members on Substack.

I recently finished the first draft of my upcoming book, and my goal is to build a beta-reader community to help shape the book and receive early feedback for the editing phase leading up to the 2026 launch.

Why this is important: building my audience and community is essential to support the upcoming book launch. Even with a publisher, it often falls to the author to market and promote the book.

Goal #2: Fall back in love with my early morning routine

Why this is important: An early morning routine sets the tone for my day. Earlier this year, I was laser-focused on writing the book, which involved late nights and a lot of night-owling. As a result, I fell out of my morning routine, and it started affecting my motivation and energy levels.

With Divina’s feedback, here is how I translated it into specifics:

“Re-establish an early morning routine that feels enjoyable and nourishing by waking up consistently at 6:30 am at least 4 days a week. I will spend the first 20 minutes on yoga, 30 minutes on meditation, and 10 minutes on free writing.”

Let’s break it down:

Specific: wake up at 6:30 am, practice meditation/yoga for 1 hour
Measurable: track this goal in the GoalsWon app and review progress with Divina
Attainable: 4 days a week, not 7 to start.
Relevant: a nourishing 1-hour routine helps me feel and be at my best during the day.
Time-bound: do this for 1 month.

Goal #3: Build strength by doing 3 weightlifting workouts per week at the gym

Why it is important: I want to grow my life force (annual goal), feel great in my body, enjoy activities like surfing, and support my vitality and long-term health. Strength training works best for my fitness and wellness, but this year I fell out of my lifting routine and struggled to reestablish consistency at the gym.

Earlier this year, I ran a half-marathon with my partner, which was a fantastic win for the team, and I was happy to finish with my best time. The caveat is that while I was training for the half, I mainly focused on cardio and neglected strength training, so even though my running improved, I lost muscle and somehow also gained a few pounds. Thanks to all those celebratory croissants and tacos!

Divina and I started working on this goal by giving it more detail and structure:

Refined Gym Win Goal:

Work out at the gym three times a week, following my exercise plan, fitness app workouts, and applying progressive overload. I will focus on feeling every movement and keeping good form. I will measure my progress by an in-body composition scan in 4 weeks (completed!)

How Goals Are Achieved with GoalsWon

Daily Support — What Makes GoalsWon Stand Out

Daily Support means your coach responds to and supports your goals every single day, including weekends.

I believe that daily support and human-to-human accountability are the secret sauce that makes GoalsWon stand out among other solutions.

Every day, I would go to the GoalsWon app to check in on my goals and briefly summarize my day: what went well and what my challenges were, how I felt and what I focused my energy on.

I would normally submit my day to Divina in the evening, and by the time I woke up in the morning, I would get messages back from her. It was so helpful to establish a consistent coaching routine I could rely on.

Coaching Calls — Weekly Touchpoints That Keep You On Track

GoalsWon offers several ways to connect and get coached. During my trial, they rolled out a new feature: weekly calls with the coach, which I found helpful alongside onboarding and monthly strategy calls.

Goalswon live coaching call with a coach

Accountability — Motivation That Feels Personal

Divina would check in on my progress daily, give me valuable feedback and encouragement. I enjoyed the motivational quotes and affirmations she shared with me.

On days when my energy or motivation dipped, she helped me reconnect to my why and used strength-based coaching to focus on what was going well. She reminded me that missing one morning routine didn’t mean the whole day was ruined. It really helps to have a coach hold up a mirror to your strengths and affirm them.

Holiday Mode and Rest Days — Real Life Included

It’s essential to be flexible and include rest days to allow for recovery and reset. After the first 10 days of coaching and daily accountability, we decided to make Sunday a rest and reset day. I would set my Sunday “goal” to be Rest: surfing with friends, reading, making a slow breakfast at home, movie night, or low-impact yoga.

Interestingly, when I scheduled a rest day on my calendar, it was more restful.

Takeaway: Quality rest that helps reset deserves to be an important goal in its own right.

Data-Driven Insights and Feedback

Another pleasant surprise was smart Coaching Insights and what my data revealed after 21 Days. Divina noticed that “based on the month, Tuesdays and Wednesdays are the toughest days for me to start my morning earlier” and asked me to reflect on anything recurring that might explain why. We then discussed strategies to avoid letting my late-night work tendencies disrupt my morning.

For example, when Divina invited me to reflect on something I had learned myself from the week, I suddenly got new clarity and insight into my early morning goal and its underlying purpose.

I realized that my early morning routine means much more to me than just starting my day off right and not having to rush. It enables a powerful mindset shift: from a deficit-based mindset (waking up late and feeling rushed by my to-do list, inbox, and phone) to one of abundance. From feeling like I’m already behind and catching up for the rest of the day to feeling like I’m ahead and have enough of everything.

When I wake up an hour earlier than I need to, I give myself extra time and space to do what supports me and to move through my day the way I want. It gives me more sense of agency and opens up new possibilities beyond a busy inbox, meetings, and checklists. With this abundance mindset, even bigger goals start to feel more achievable. I even gave this routine a name: The Morning Sync, and I plan to include it in my book.

Visual Progress

For visual learners like me, seeing your progress can be a huge boost to keep you going.

GoalsWon provides clear charts and graphs to show your progress.

Every day, Divina shared my progress snapshot with me, visualized across my main goals and habits that we were tracking. It makes it easier to see how small daily steps compound to real growth and behavior change.

Wins & Celebrations

Thanks to my coach, I realized that I need to celebrate my successes and wins, even the smallest ones, more often. Sometimes I don’t even acknowledge them as wins.

For example, I shared with Divina that on one of the weekends, I ran a 5-mile race in support of Mental Health awareness in our neighborhood in Ocean Beach. Just as something that we did over the weekend. Not a big deal, in my mind.

Divina acknowledged it as a win and even created a celebratory milestone with a cool graphic, which was great to see!

Celebrating small wins keeps me motivated and gives me the energy to keep pushing toward my goals. And it’s not just a nice feeling, it’s actually how the brain works. When we reward ourselves, our brain releases dopamine, which motivates us to repeat that behavior.

Intuitive and Pleasant App Experience

I enjoyed the user-friendly interface of the app. Nothing is too distracting, and everything is designed to help stay focused on goals and communication with the coach. GoalsWon is available on both the App Store and Google Play.

Here are the main screens in the app:

Goals Screen: my goals command center, where I can see my top priorities for the day. At the bottom, there’s a big button to submit my day to the coach.

The Targets screen is where I set up my monthly and yearly goals.

The Milestones screen (my favorite): my coach updated it based on my progress and notable events, helping make success more visual and rewarding!
Chat with Coach: I can easily access the chat with my coach to share my thoughts, ask questions, submit a photo, and check the coach's status to see her recent highlights or the goals she has been focusing on. It was great to work toward some of the lifestyle goals we both shared, like improving certain sleep habits.

My Results After 3 Weeks with GoalsWon

At the end of the month, my coach shared a concise summary outlining my wins, key insights, and areas for improvement.

Key highlights from the coach:

☀️ You've worked on growing your business 83% of the time this month.
☀️ Morning routine is at 61% this month, 11 days out of 18. Not bad for a start. Most consistent on Thursdays, followed by Fridays!
☀️ Wrapping up work on time was achieved 93% of the time, showing the best consistency with this goal. 🙌
☀️ Lastly, book work is mostly correlated with wrapping up your work by 7 PM. This means when you work on your book, you also end on time! Similar to book work and exercise, when you do your exercise, you are more likely to work on your book and vice versa!

Key highlights from me:

Goal #1: Book Launch and Community Growth Goal

I dreaded this goal! But we were able to flip that around with the support of my coach, and now I actually enjoy inviting people into what I’m building—huge win for me.

I grew my newsletter community on Substack from 0 to 150 members during the trial, and it has been steadily growing since.

Divina helped me break through my initial resistance, and by the end of the month, I was genuinely having fun connecting with people and inviting them into my book adventure. Thank you for believing in me, Divina.

Chat conversation with a coach on a mobile app interface

Extra bonus: I reconnected with some people I hadn’t spoken to in years and felt supported on my book journey. I got the chance to catch up on their lives and see how we can support each other’s work.

Goal #2: Fall back in love with my early morning routine

Early mornings are still challenging for me but I was able to stick with my morning routine 3 out of 4 days on average and go to bed at a more consistent time. Significant improvement and a move in the right direction.

Breakthrough moment: I defined to myself why it is important to me and how that supports all other areas of my life, especially during stressful times. I created a new morning ritual: the Morning Sync, which I will be incorporating in my book.

Goal #3: Build strength by doing 3 weightlifting workouts a week at the gym

We did it! I hit the gym three times a week and rediscovered my motivation, as well as the joy of showing up and honoring my body with a good workout. This is the first time in the last 12 months that I made it to the gym 12 times a month, and this habit is now successfully re-established.

In-body scan results showed that I gained more strength (lean body mass), improved my body composition, and metabolism. I have much more energy now, too, which aligns with my yearly goal of growing my life force.

I credit this win to having a coach in my corner every day and using GoalsWon to track progress, reflect, and get real-time feedback—without the typical delay between weekly sessions.

GoalsWon vs Headspace vs ChatGPT Coaching: Which Coaching App Wins?

If you’re comparing GoalsWon vs. Headspace—or even human-based coaching apps vs. AI-based coaching—here’s a quick Coaching App Comparison.

Comparison table of three digital coaching apps — GoalsWon, Headspace, and ChatGPT — showing differences in daily support, human coaches, supporting tools, live calls, text chats and monthly cost

Key Takeaways & Value

Most of my past coaching experience was face-to-face, usually in weekly sessions. It was helpful, but I tended to use it in short bursts whenever I needed an extra push for my business goals as a startup founder.
I used to believe that coaching presence—being in the same room or live on a call—was essential for it to work. Otherwise, I thought, why not just let ChatGPT coach me all day, right? Turns out, not at all. What surprised me most was how effective asynchronous coaching could be when it combined daily support, accountability, and optional live calls. Through quick, consistent text check-ins, I actually felt my coach’s presence more often, which helped me build steady momentum day by day.
One of the biggest benefits was how my coach and the app together helped me focus my attention. That focus became a driving force behind achieving my goals. As Dr. Rick Hanson, neuropsychologist, puts it, “Where attention goes, energy flows.”
Value: GoalsWon plans start at around $90/month. At first, that might sound steep for an app subscription, but compared to the cost of hiring a traditional coach, it’s a strong investment in yourself and your goals. Annual plan offers the best value at less than $60/month.
If you’re someone who values face-to-face connection, GoalsWon still has you covered with weekly or monthly live calls, so you can shape the coaching experience to fit your lifestyle.
Finally, coaching is a relationship—it deepens over time. As Divina and I got to know each other, the support felt more personal, intuitive, and motivating week after week.

GoalsWon Coaching Plans

Monthly: $90/mo (7-day free trial). Weekly calls add-on: +$60/mo.
Annual: $60/mo (14-day free trial). Weekly calls add-on: +$40/mo.

Bottom Line

GoalsWon bridges the best of both worlds—the warmth of human coaching and the consistency of a digital accountability app, making it a powerful hybrid for anyone serious about personal growth.

Like anything worth building, it takes time. Give yourself (and your coach) at least a month to find your rhythm, build new habits, and feel the real impact of daily accountability and human support.

Ready to invest in your growth and finally move forward on those goals you’ve been stuck on? Start your free 7-day GoalsWon trial her e and see what a little daily accountability can do.

This post is created in collaboration with GoalsWon and may contain affiliate links. All opinions, experiences, and recommendations are my own.

About Author

Ollie is a California-based mindfulness meditation teacher and wellness coach with a globally inspired practice. Formerly an e-commerce executive, she founded Meditate Mate and co-founded Inward VR, a mindfulness technology startup. Her down-to-earth approach to mental and physical wellness combines meditation, weightlifting, yoga, and surfing.